Un-hopeful is a word that is often used to describe a person or situation that lacks optimism or positivity. Some synonyms for un-hopeful include pessimistic, despondent, discouraging, bleak, and negative. Pessimistic describes a person who always expects the worst to happen, while despondent refers to a feeling of extreme sadness or hopelessness. Discouraging suggests that a situation or person causes one to lose hope, while bleak implies a lack of hope or encouragement. Negative describes someone who constantly focuses on the drawbacks rather than the positives in a situation. All of these synonyms can be used interchangeably with un-hopeful to describe a situation or person who lacks hope.